👻 The Loneliness Tax and Other Remote Work Phantoms Costs

Hello there 😎 

My manager asked me how I felt moving from Dublin to Philadelphia.

I didn’t hesitate.

The answer seemed to surprise him.

Look: I loved life in Ireland. I'm grateful my family had the opportunity to live and work abroad.

But I was glad my time zone aligned with the rest of the company’s again. No more 8 PM strategy sessions or 5 AM stand-ups.

The time difference had taken its toll.

Here's what you'll learn today:

• 15 companies hiring remotely in finance (with growth & employee satisfaction data)

• How to make your work visible and get recognized in a remote role

• How to prevent “the WFH time trap” and set yourself up for better work-life balance

…and more!

Let’s jump in.

✨ Remote Work Is the Best Thing That's Happened to My Career

Since I started working remotely 11 years ago, I’ve:

• Walked my kids to school nearly every day

• Moved every 2 years and lived in LA, NYC, and Dublin, Ireland

• Worked at companies like I Will Teach, Reforge, Noom, & Persefoni

In my opinion, remote work is a critical step in the New Career path.

But the remote work community tends to focus only on the positives of remote work.

There's a lot of cheerleading and celebration of remote work without acknowledging its real challenges.

We need to have honest conversations about both its benefits and drawbacks.

🤫 There Are Realities of Remote Work We Don't Talk About

This is a mistake.

Getting a remote job might seem like the answer to all your work-life challenges. But that’s an illusion.

Working remotely brings its own set of challenges that you don't discover until you're actually doing it. I call these the “phantom costs” of remote work.

Here are the six phantom costs of remote work people don’t talk about:

1/ The end of over-the-shoulder learning

There are a lot of things I think Steve Jobs got wrong. But I think he got this one right. He said:

Excellence is something you observe, then work to achieve.

And it’s harder to observe excellence when working remotely versus in-person.

My first job in Hollywood was at a literary agency. The most valuable education came from watching the top performers: how they spoke to clients, negotiated deals, and managed difficult conversations.

I don’t think you can replicate this "over-the-shoulder" learning in a remote setting—It doesn’t matter how many Zoom calls you have.

(Exception to the rule: I learned a sh*t ton from Daniel Wolchonok over Zoom.)

But there are still ways to maximize your learning opportunities:

2/ The WFH time trap

This still happens to me every week.

I'll start working. Then I’ll notice the pile of laundry in the corner. "I'll just quickly throw that in," I think.

While I'm up, I spot the dishes in the sink. "Might as well clean those too."

Then Amy asks for help with something.

Next thing I know, I've spent an hour on household tasks instead of work.

I call this "the WFH time trap." Your work time slowly drains away into other activities.

This is a feature, not a bug of remote work. It's awesome to have the flexibility to handle life’s errands. But small interruptions can seriously derail your productivity, especially during deep work sessions.

The good news is that once you recognize this pattern, you can prepare for it.

3/ Remote work’s glass ceiling

A month into her new job, my client sent me a WhatsApp message:

She was an IC on a siloed team. She was worried about her career growth.

This is a challenge I’ve seen over and over again.

When you're not physically present in an office, your contributions can go unnoticed. Casual conversations where you humble brag about your wins don't happen.

In a traditional office, people might notice you staying late to finish a project or see you collaborating with colleagues. In a remote setting, all of that becomes invisible unless you intentionally make it visible.

4/ Your professional network is quietly fading

My friend landed a remote role at a tech startup in 2022: great pay, full flexibility, and more time with his young kids. It was perfect.

Until the shoe dropped in 2024. Company layoffs. He scrambled to find his next thing. And he realized: his professional network had quietly faded away.

The casual coffee chats, conference connections, and meetups that used to fill his calendar disappeared over the past 18 months.

Here’s a hard truth about remote work:

It ENABLES productivity at the COST of serendipity.

Those chance encounters, spontaneous conversations, and in-person connections that shape your career and personal growth become rare.

Some experiences just can't be replicated through a screen.

No matter how good your Zoom setup is or how advanced your collaboration tools are, certain interactions - like mentorship, celebrations, and iterative feedback - are fundamentally different in person.

To maintain your professional network while working remotely, you need to work on it with intention.

5/ A remote work office never closes

In Dublin, I worked at split day. It looked something like this:

• 5:00-7:00 AM: Log in, catch up on emails and Slack messages from US team

• 7:00-8:30 AM: Get kids ready, breakfast, school drop-off

• 8:30-9:30 AM: Gym

• 10:00-2:00 PM: Deep work, meetings with US team starting their day

• 2:00-3:30 PM: Break, household tasks, quick errands

• 3:30-4:30 PM: School pickup, kids' activities

• 5:00-7:00 PM: Family dinner, kids' homework

• 8:00-10:00 PM: Back online for US team's afternoon meetings

Remote work doesn't mean less work - it means different work patterns. And sometimes, these patterns can be more demanding than a traditional 9-5 office schedule.

(Gina Sapién wrote a great post on this.)

With a split schedule, work is constantly present in your mind - there's never a true "off" switch. You never get to shut down. It sucks.

Be prepared to solve for this.

6/ The loneliness tax

My presentation was scheduled for 8 PM.

At 10 AM, I had exactly zero slides completed. I was completely stuck.

I started wandering around Brooklyn, searching for ideas. It felt like my career was crumbling. I started fantasizing about alternative careers—maybe I could become a dog walker instead?

The hardest part? I felt like I was completely and utterly alone.

Remote work can amplify feelings of isolation in ways that catch us off guard.

When you're struggling with a project or facing a creative block, the physical distance from your colleagues feels like an ocean between you and anyone who can help.

The loneliness tax of remote work takes a real toll on both our mental well-being and professional performance. The key is being proactive about building your support system.

💫 The Bottom Line

Remote work comes with six phantom costs that aren't immediately obvious:

1. The end of over-the-shoulder learning

2. The WFH time trap

3. Remote work’s glass ceiling

4. Your professional network is quietly fading

5. A remote work office never closes

6. The loneliness tax

The key is being intentional about managing these hidden costs.

None of these are dealbreakers. They're just challenges to plan for.

Start by assessing which costs impact you most. If you're early in your career, the lack of mentorship might outweigh the benefits of flexibility. For mid-career professionals, the ability to design your own schedule might be worth the extra effort needed to maintain visibility.

Remote work isn't about avoiding costs - it's about choosing which tradeoffs align with your goals, whether that's accelerated learning, family time, or career advancement.

Acknowledge and plan for the phantom costs.

Then you can build a remote work life that truly works for you.

I love meeting new people. Say hi on LinkedIn 👋

That’s a wrap. See you next week 👋